ES2199434T3 - CHEMICAL COMPOSITIONS. - Google Patents
CHEMICAL COMPOSITIONS.Info
- Publication number
- ES2199434T3 ES2199434T3 ES98913569T ES98913569T ES2199434T3 ES 2199434 T3 ES2199434 T3 ES 2199434T3 ES 98913569 T ES98913569 T ES 98913569T ES 98913569 T ES98913569 T ES 98913569T ES 2199434 T3 ES2199434 T3 ES 2199434T3
- Authority
- ES
- Spain
- Prior art keywords
- indicator
- component
- components
- weight
- polyol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title description 7
- 239000000126 substance Substances 0.000 title description 2
- 229920005989 resin Polymers 0.000 claims abstract description 5
- 239000011347 resin Substances 0.000 claims abstract description 5
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 4
- 239000007793 ph indicator Substances 0.000 claims abstract description 3
- 229920005862 polyol Polymers 0.000 claims description 11
- 150000003077 polyols Chemical class 0.000 claims description 11
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- FRPHFZCDPYBUAU-UHFFFAOYSA-N Bromocresolgreen Chemical compound CC1=C(Br)C(O)=C(Br)C=C1C1(C=2C(=C(Br)C(O)=C(Br)C=2)C)C2=CC=CC=C2S(=O)(=O)O1 FRPHFZCDPYBUAU-UHFFFAOYSA-N 0.000 claims description 3
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 claims description 3
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 claims description 3
- WWAABJGNHFGXSJ-UHFFFAOYSA-N chlorophenol red Chemical compound C1=C(Cl)C(O)=CC=C1C1(C=2C=C(Cl)C(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 WWAABJGNHFGXSJ-UHFFFAOYSA-N 0.000 claims description 3
- 229960003531 phenolsulfonphthalein Drugs 0.000 claims description 3
- OBRMNDMBJQTZHV-UHFFFAOYSA-N cresol red Chemical group C1=C(O)C(C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C=C(C)C(O)=CC=2)=C1 OBRMNDMBJQTZHV-UHFFFAOYSA-N 0.000 claims description 2
- XJRPTMORGOIMMI-UHFFFAOYSA-N ethyl 2-amino-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N)=NC=1C(F)(F)F XJRPTMORGOIMMI-UHFFFAOYSA-N 0.000 claims description 2
- PRZSXZWFJHEZBJ-UHFFFAOYSA-N thymol blue Chemical compound C1=C(O)C(C(C)C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C(=CC(O)=C(C(C)C)C=2)C)=C1C PRZSXZWFJHEZBJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002184 metal Substances 0.000 abstract 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 7
- 229920005863 Lupranol® Polymers 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 2
- MKNQNPYGAQGARI-UHFFFAOYSA-N 4-(bromomethyl)phenol Chemical compound OC1=CC=C(CBr)C=C1 MKNQNPYGAQGARI-UHFFFAOYSA-N 0.000 description 2
- 235000004443 Ricinus communis Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 229910000514 dolomite Inorganic materials 0.000 description 2
- 239000010459 dolomite Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000003856 thermoforming Methods 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- XVRFLAKLFMLOPO-UHFFFAOYSA-N 3-hydroxy-5-methyl-1h-pyrimidine-2,4-dione Chemical compound CC1=CNC(=O)N(O)C1=O XVRFLAKLFMLOPO-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
Abstract
Sistema de envase múltiple que comprende dos o metálic componentes que reaccionan conjuntamente para formar una resina termoendurecible, caracterizado porque uno de los componentes contiene hasta un 0,01% en peso de un indicador de pH.Multiple container system comprising two or metal components that react together to form a thermosetting resin, characterized in that one of the components contains up to 0.01% by weight of a pH indicator.
Description
Composiciones químicas.Chemical compositions
El presente invento se refiere a sistemas que reaccionan para producir resina termofraguante, comprendiendo el sistema un poliol en un componente y un isocianato como un segundo componente y hasta 0,01% en peso de un indicador de pH en uno de dichos componentes.The present invention relates to systems that react to produce thermosetting resin, comprising the system a polyol in one component and an isocyanate as a second component and up to 0.01% by weight of a pH indicator in one of these components.
Las resinas termofraguantes tal como poliuretanos y resinas epoxi se utilizan ampliamente, por ejemplo como adhesivos, para obtener revestimientos y en aplicaciones de herramientas. En muchos casos la mezcla de los componentes es muy similar en apariencia a algunos o todos los componentes individuales. Es por tanto posible producir productos en donde se omite uno o mas componentes, por ejemplo debido a la interrupción de la máquina, y pasar inadvertido al operario este evento.Thermosetting resins such as polyurethanes and epoxy resins are widely used, for example as adhesives, to obtain coatings and in applications of tools In many cases the mixing of the components is very similar in appearance to some or all components individual. It is therefore possible to produce products where omit one or more components, for example due to interruption of the machine, and pass this operator inadvertently.
En algunos casos se adiciona un colorante o pigmento a un componente y luego es posible asegurar la mezcla apropiada observando el color de la mezcla, y comparándolo con el color del componente individual. Esto requiere normalmente de 0,1 a 5% de costoso colorante o pigmento.In some cases a dye or pigment to a component and then it is possible to ensure the mixture appropriate observing the color of the mixture, and comparing it with the color of the individual component. This normally requires 0.1 to 5% expensive dye or pigment.
Hemos encontrado ahora, sorprendentemente, que una cantidad muy reducida de un compuesto que se utiliza normalmente como un indicador de cambio de pH, exhibe también un cambio de color en los sistemas termofraguantes.We have found now, surprisingly, that a very small amount of a compound that is used normally as an indicator of pH change, it also exhibits a color change in thermoforming systems.
Así pues, el presente invento proporciona un sistema multi-envase que comprende dos o mas componentes que reaccionan entre sí para formar una resina termofraguante, cuyo sistema comprende un poliol en un componente y un isocianato como un segundo componente y hasta 0,01% en peso de un indicador, caracterizado porque el indicador es un indicador de pH que produce un cambio de color cuando se mezclan los componentes y está presente en el componente poliol.Thus, the present invention provides a multi-container system comprising two or more components that react with each other to form a resin thermoforming agent, whose system comprises a polyol in one component and an isocyanate as a second component and up to 0.01% by weight of an indicator, characterized in that the indicator is an indicator of pH that produces a color change when the components are mixed and is present in the polyol component.
Usualmente el sistema del invento comprenderá dos envases, cada uno de los cuales contiene un componente reactivo.Usually the system of the invention will comprise two packaging, each of which contains a component reagent.
Solo se precisan cantidades muy pequeñas de indicador para producir un cambio de color deseado. Usualmente es suficiente menos de 0,01% en peso del componente al que se adiciona. De preferencia la cantidad se encuentra entre 0,0003% y 0,006%, y mas preferentemente entre 0,0005% y 0,004%.Only very small amounts of indicator to produce a desired color change. Usually is sufficient less than 0.01% by weight of the component to which add. Preferably the amount is between 0.0003% and 0.006%, and more preferably between 0.0005% and 0.004%.
El indicador puede adicionarse a cualquier componente siempre que no reaccione con dicho componente y así impedir el cambio de color.The indicator can be added to any component as long as it does not react with that component and so Prevent color change.
Muchos indicadores, tal como los que contienen uno o mas grupos fenólicos, reaccionarán con isocianatos con lo que se destruye el cromóforo. En este caso el indicador debe adicionarse al componente poliólico.Many indicators, such as those containing one or more phenolic groups will react with isocyanates with what The chromophore is destroyed. In this case the indicator must add to the polyol component.
Puede utilizarse cualquier indicador que produzca un cambio de color cuando se mezclan los componentes. Sin embargo el indicador es de preferencia uno que, en sistemas acuosos, empiece a cambiar el color por lo menos a un pH inferior a 8,2. Se prefieren especialmente aquellos que se colorean fuertemente en estados ácido y alcalino o aquellos que dan un fuerte color alcalino a valor pH bajos, por ejemplo inferiores a 5,0. Como ejemplos de indicadores apropiados puede citarse Cresol Red, Bromophenol Blue, Bromocresol Green, Bromocresol Purple, Chlorophenol Red, Phenol Red y Thymol Blue.Any indicator that produces a color change when the components are mixed. Nevertheless the indicator is preferably one that, in aqueous systems, Start changing the color at least at a pH below 8.2. I know they especially prefer those that are strongly colored in acid and alkaline states or those that give a strong color low pH alkaline, for example less than 5.0. How Examples of appropriate indicators can be cited Cresol Red, Bromophenol Blue, Bromocresol Green, Bromocresol Purple, Chlorophenol Red, Phenol Red and Thymol Blue.
Debe apreciarse que el cambio de color observado no es siempre el mismo en diferentes sistemas y no es también siempre el mismo que el cambio de color producido con el cambio del pH en un sistema acuoso. Por ejemplo Chlorophenol Red cambia de naranja a beige en sistemas poliuretánicos. Cuando se indica un cambio de pH el color cambia de amarillo a rojo.It should be noted that the observed color change it is not always the same in different systems and it is not also always the same as the color change produced with the change of pH in an aqueous system. For example Chlorophenol Red changes from Orange to beige in polyurethane systems. When a pH change the color changes from yellow to red.
Cuando se mezclan los dos componentes, la persona que lleva a cabo la operación puede ver fácilmente a partir del cambio de color que los dos componentes se han mezclado, y que la mezcla es uniforme a través de la mezcla.When the two components are mixed, the person who performs the operation can easily see from the color change that the two components have mixed, and that the Mix is uniform throughout the mix.
El invento se ilustra por medio de los ejemplos siguientes.The invention is illustrated by means of the examples. following.
Ejemplos 1-6Examples 1-6
Se prepara poliuretanos a partir de un componente poliólico (A) y el componente (B) que es 4,4'-metilen difenil diisocianato líquido semidestilado (MDI) en una relación de (A):(B) de 100:25 en peso. El componente (A) tiene la composición:Polyurethanes are prepared from a component polyol (A) and component (B) which is 4,4'-methylene diphenyl diisocyanate liquid semi-distilled (MDI) in a ratio of (A) :( B) of 100: 25 by weight. The component (A) has the composition:
\newpage\ newpage
Se adicionan indicadores al componente (A) como una solución al 0,1% en un vehículo apropiado que es aceite de ricino o un poliol (Lupranol 1000, BASF). Se obtienen los resultados siguientesIndicators are added to component (A) as a 0.1% solution in an appropriate vehicle that is oil from castor or a polyol (Lupranol 1000, BASF). You get the following results
Ejemplos 7-9Examples 7-9
Siguiendo el procedimiento de los ejemplos 1-6 donde los ingredientes son como se expone a continuación, siendo MDI el componente (B) y el resto es el componente (A), obteniéndose el cambio de color con la adición de (B) a (A) como se ha expuesto.Following the procedure of the examples 1-6 where the ingredients are as exposed to then, being MDI the component (B) and the rest is the component (A), obtaining the color change with the addition of (B) to (A) as stated.
(Continuación)(Continuation)
Ejemplos 10-13Examples 10-13
Se utilizan diferentes cantidades de indicador en un sistema poliuretánico para mostrar los diferentes cambios de color. Los ingredientes utilizados y los cambios de color son como sigue:Different amounts of indicator are used in a polyurethane system to show the different changes of color. The ingredients used and the color changes are like follow:
Claims (3)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9706223.6A GB9706223D0 (en) | 1997-03-26 | 1997-03-26 | Chemical compositions |
| GB9706223 | 1997-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2199434T3 true ES2199434T3 (en) | 2004-02-16 |
Family
ID=10809865
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES98913569T Expired - Lifetime ES2199434T3 (en) | 1997-03-26 | 1998-02-20 | CHEMICAL COMPOSITIONS. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6060544A (en) |
| EP (1) | EP0970133B1 (en) |
| JP (1) | JP2001518973A (en) |
| AT (1) | ATE240358T1 (en) |
| CA (1) | CA2284841A1 (en) |
| DE (1) | DE69814604T2 (en) |
| ES (1) | ES2199434T3 (en) |
| GB (1) | GB9706223D0 (en) |
| ID (1) | ID22634A (en) |
| TW (1) | TW496888B (en) |
| WO (1) | WO1998042762A1 (en) |
| ZA (1) | ZA982513B (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19928676A1 (en) * | 1999-06-23 | 2000-12-28 | Basf Ag | Polyisocyanate poly-addition product, e.g. flexible polyurethane foam for cushions and padding, contains hydrophobic compounds and other special modifiers, e.g. metal salt, anhydride, sulfone or unsaturated acid |
| DE10115004A1 (en) * | 2001-03-26 | 2002-10-10 | Input Inst For Polyurethane Te | Control of moisture induced curing of polyurethane foam with a pH indicator, useful for curing foamed assembly materials, adhesives, and jointing compounds ensures adequate curing by following the color change with increase in pH |
| DE102008019017B3 (en) * | 2008-04-15 | 2009-12-31 | Mankiewicz Gebr. & Co. Gmbh & Co Kg | Curable compositions containing color indicators for indicating the curing progress and methods for indicating the curing progress of these curable compositions |
| US8975312B2 (en) * | 2010-06-29 | 2015-03-10 | 3M Innovative Properties Company | Color indicating epoxy resins and methods thereof |
| US20160151251A1 (en) * | 2012-12-20 | 2016-06-02 | Kao Germany Gmbh | Aqueous oxidizing composition |
| JP2018502179A (en) | 2014-11-18 | 2018-01-25 | スリーエム イノベイティブ プロパティズ カンパニー | Discoloring adhesive composition |
| CN112480370A (en) | 2015-03-19 | 2021-03-12 | 泽费罗斯股份有限公司 | Esterified acids for polymeric materials |
| KR102780994B1 (en) * | 2018-02-22 | 2025-03-14 | 신에쓰 가가꾸 고교 가부시끼가이샤 | Room temperature curable organopolysiloxane composition, structure and method for determining the curing state of the composition |
| JP7265242B2 (en) * | 2018-12-10 | 2023-04-26 | 国立研究開発法人宇宙航空研究開発機構 | RESIN COMPOSITION, METHOD FOR PREDICTING FAILURE OF CURE, METHOD FOR MANUFACTURING JOINTED BODY, ADHESION KIT, AND DETERMINATION OF DEFAULT-CUREMENT |
| AU2020256063B2 (en) | 2019-04-03 | 2022-06-02 | Zephyros, Inc. | Two-part phosphate ester epoxy composition |
| CN118176229A (en) * | 2021-10-29 | 2024-06-11 | 泽菲罗斯有限公司 | Reaction-induced color-changing composition |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT650412A (en) * | 1960-03-17 | |||
| US3773706A (en) * | 1971-11-26 | 1973-11-20 | Ubm Armonk | Method for indicating stage of cure of crosslinked resins and compositions resulting therefrom |
| JPS51109999A (en) * | 1975-03-25 | 1976-09-29 | Sumitomo Electric Industries | EHOKISHIJUSHINOKOKAHOHO |
| US4160064A (en) * | 1977-06-15 | 1979-07-03 | Theodore R. Flint | Epoxy adhesive sealant |
| US4164492A (en) * | 1978-03-14 | 1979-08-14 | Alco Standard Corporation | Novel catalyst for curing polyester resins and method for determining the degree of cure in polyester and epoxy resin systems |
| CH665483A5 (en) * | 1985-11-22 | 1988-05-13 | Coltene Ag | METHOD FOR CONTROLLING THE HOMOGENEOUS MIXING OF A HAIRABLE MATERIAL AND A HARDENABLE MASS FOR CARRYING OUT THE METHOD. |
| FR2630743B1 (en) * | 1988-04-29 | 1990-08-31 | Gosselin Claude | METHOD FOR SEALING BY INJECTION OF AN ACRYLAMIDE-BASED MIXTURE AND CORRESPONDING MIXTURE |
| US5607644A (en) * | 1993-06-10 | 1997-03-04 | Optical Sensors Incorporated | Optical sensor for the measurement of pH in a fluid, and related sensing compositions and methods |
-
1997
- 1997-03-26 GB GBGB9706223.6A patent/GB9706223D0/en active Pending
-
1998
- 1998-02-20 JP JP54479398A patent/JP2001518973A/en active Pending
- 1998-02-20 ID IDW991043A patent/ID22634A/en unknown
- 1998-02-20 CA CA002284841A patent/CA2284841A1/en not_active Abandoned
- 1998-02-20 WO PCT/EP1998/000979 patent/WO1998042762A1/en not_active Ceased
- 1998-02-20 EP EP98913569A patent/EP0970133B1/en not_active Expired - Lifetime
- 1998-02-20 DE DE69814604T patent/DE69814604T2/en not_active Expired - Fee Related
- 1998-02-20 AT AT98913569T patent/ATE240358T1/en not_active IP Right Cessation
- 1998-02-20 ES ES98913569T patent/ES2199434T3/en not_active Expired - Lifetime
- 1998-02-24 TW TW087102586A patent/TW496888B/en active
- 1998-03-18 US US09/040,989 patent/US6060544A/en not_active Expired - Fee Related
- 1998-03-25 ZA ZA982513A patent/ZA982513B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO1998042762A1 (en) | 1998-10-01 |
| TW496888B (en) | 2002-08-01 |
| GB9706223D0 (en) | 1997-05-14 |
| DE69814604D1 (en) | 2003-06-18 |
| DE69814604T2 (en) | 2004-04-29 |
| CA2284841A1 (en) | 1998-10-01 |
| EP0970133A1 (en) | 2000-01-12 |
| EP0970133B1 (en) | 2003-05-14 |
| JP2001518973A (en) | 2001-10-16 |
| ZA982513B (en) | 1998-09-28 |
| US6060544A (en) | 2000-05-09 |
| ID22634A (en) | 1999-12-02 |
| ATE240358T1 (en) | 2003-05-15 |
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